Reaktion #307425

ord-7f17c702daed424fab6fd6d1551b886b

Reaktionsgleichung

Nc1c(O)cccc1[N+](=O)[O-]
2-amino-3-nitrophenol
O=C([O-])[O-].[K+].[K+]
K2CO3
CC(C)I
2-iodopropane
→
CC(C)Oc1cccc([N+](=O)[O-])c1N
2-isopropoxy-6-nitro-phenylamine

Edukte

Nc1c(O)cccc1[N+](=O)[O-]
2-amino-3-nitrophenol
O=C([O-])[O-].[K+].[K+]
K2CO3
CC(C)I
2-iodopropane

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated in vacuo
  2. 2
    Extraktionextracted with EtOAc (3 times)
  3. 3
    Waschenwashed with water, brine
  4. 4
    Trocknendried over MgSO4
  5. 5
    Einengenconcentrated in vacuo
  6. 6
    SonstigePurification by CC with EtOAc-Hept (2:8)

Vorschrift

To a solution of 5 g of 2-amino-3-nitrophenol in 10 mL DMF were added 4.9 g of K2CO3 and 3.6 mL of 2-iodopropane. The reaction mixture was stirred at rt overnight and then concentrated in vacuo. The residue was taken up in sat. aq. NH4Cl and extracted with EtOAc (3 times). The organic phases were combined, washed with water, brine, dried over MgSO4 and concentrated in vacuo. Purification by CC with EtOAc-Hept (2:8) afforded 5.2 g of 2-isopropoxy-6-nitro-phenylamine as orange oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08202885B2uspto-grants-2012_06